Are you living your best life today? From 1 to 10. How would you improve it.

• Joe: 8 or 9. I would exercise and meditate more.
• Matt: currently 6 but moving to an 8. Stressed with work. Trying to be better about delegating to other leaders. Goal to move things off the plate.

Follow up: What’s getting in the way of getting to 10?

• Streaming TV gets in the way of sleeping. A few too many hobbies.
• The goal post is always moving, but it’s important to remember it’s only a game.

Follow up: What are the qualities or values of the people you’re delegating to that’s helpful?

• Both of us have built great teams around us.
• Matt: We have a Southworth board member who is great – she’s a go-getter and a doer. It’s helpful to constantly try to make the team better, stronger. I wasn’t always doing that. Now, I consistently add to my plate. As soon as I move something off, I’m looking for my next company. I’m learning to off-load on someone else.

As you build great teams, what are the characteristics you look for in those team members? How do you determine who’s great for the team?

• We need more people who communicate in a like manner: to take what you’ve said and play it back so that they understand it.
• Bring solutions, not problems. Even if it’s not the right one, you can talk about a solution instead of solving the problem for them.
• CEO of Jefferies put out a top 100 list has a lot of team-related nuggets that are very helpful.
• We’re looking for people who are energized by the work and by tough problems.
• Having common sense is a key component to making the “Joe & Matt team.”

When you think about three generations out, what comes to mind? What is your optimal view of the family support? How would you like to see them living and what are their values?

• Matt: Having a positive impact on the world, that can still be profitable. You don’t want the money to hinder them, and you also want to consider the benefit to the world.
• Joe: As Warren Bufffet says “Enough so they don’t have to worry, but not so much that they don’t have to work.”

Is there a number? How much is too much?

• Matt: There is not right answer. For some an amount will make them happy, for others it is just subsistence. You also want to leave flexibility to reward and support your children. And you want to be careful because it makes things complicated when people feel they didn’t get their fair share or someone got more.
• Joe: I don’t think about it a lot. I don’t think that my progeny will be a reflection of me – I don’t know who these people are going to be. What I want for them is to be happy and healthy.
• Intent: live a useful life.

So, are we living with intent? Are they living a useful life. Is the family office empowering the family to do the things they want to do but not give them enough to become detrimental to themselves or the family?

• Joe: How do you define a “useful life”? Where’s the line? What is enough? I’m looking for net-positive. If fly on a private jet once in a while, are you a horrible person? I’m not looking to dictate to future generations on how they should live their lives. Just looking to provide guidance.
• Matt: no matter what, Joe’s values will be passed down in some compacity.
• Joe: my book isn’t my law. It’s how I perceived the world.

If you hadn’t created Commonwealth, what career would you have pursued?

• Joe: I took a test when I was younger and the results were that I was worst at sales, best at farming. So I’ve been pretty good at sales. I like teaching, because I like ot see that ‘a-ha’ moment in people. But, I can be happy at doing pretty much anything.

What are some meaningful experiences that you want future generations to have?

• Joe: Love; helping other people, not because it’s noble, but because it’s nourishing to us and to others’ future experiences; being in a loving relationship.
• Matt: When I moved from high school to college, I slacked off and found different parts of a career that energized and excited me and moved me to build something. It was a nourishing feeling. It’s a good reminder to hear from someone who’s done all of that who then looks back and says that the personal relationships were the valuable component.
• Joe: Some more additions: be on a high-performing team, it’s exhilarating. Find exciting people- these people are the greatest teachers.

The scale of wealth is enough that it’s going to support multiple generations. So what does net-positive mean to you?

• Joe: We all make mistakes, but I want to know that the world is better off with my being here. I also want to cultivate ideas that make the world better.

How would you want to see your stakeholders treated? Divested?

• Joe: In the event of divesting, I’d want the FAB to approach everything fairly and compassionately. Do the best thing in the moment. Everything factors into the decision. Make the hard decisions, but in a compassionate way. Personally, I want to do the smart, compassionate thing.

Matt, if you had to give away all the wealth right now, where would you want it to go?

• The question is complicated. There might be assets that are losing money on the sheet but questions to consider:
  • Does it strengthen a portfolio?
  • Does it impact the stakeholders? How does it impact the stakeholders?
• Owning a business is a great way to steward assets. But if we were to fire sale everything tomorrow, my difficulties:
  • Would we create a donor advisor fund and drip out 5% every year?
    • I don’t know if giving to solar development every year – and we don’t see benefits for another 50 years, when there’s starving people every day I could help.
  • It takes a lot of energy to deploy money, make sure it’s deployed well and with a net-positive result.
• All that to say, I don’t have the silver bullet. I don’t have a cause or a school that’s more important. The judiciousness required to give money- I don’t have that answer right now.

If you only had one thing to give money, what would be that one thing?

• Joe: Health and wellness in the western world.
• Matt: Climate-related stuff, particularly in relation to water. Climate change stories are intricate and varied.

Do you feel personal obligations to do something good for the world as opposed to something smaller?

• Matt: I’m drawn to larger, more intractable issues and gravitate to problem-solving. Tiffany has a natural skill for understanding community-dynamics.

Would you [Joe] be really bummed if Matt sold off all the businesses to focus on those issues?

• Joe: Not if he did it in a smart way. The more business we do, the broader our networks and our contacts – we should take advantage and not let it go to waste. I have interest in longevity, but probably half of the money we give to hospitals goes to current community care. It’s a good thing if we can raise the standard of healthcare in the communities where we have a footprint. It used to be just Commonwealth, but it’s grown significantly. On the philanthropic side, we have TAO Jones. We’re trying to create an ecosystem for social heroes. Very few of them are widely recognized. I’m trying to be a catalyst for that.

When your future descendants think about you, what do you want them to think of? G5 is now talking about G1 and G2- what do we hear.

• Joe: He was a good guy. They might talk about how great we were to prop up their own ego. I want them to think we were good people. We were entrepreneurs, we were creators, we were problem solvers. We loved, and we were loved.
• Matt: We don’t donate to get our names on things. Rather than thinking about me, I want them to have certain lessons or skills to take into the world. If someone can find the fun, build something, small or big, that leaves the world a bit better.
• Joe: I like Commonwealth because of the name. If we sell the company, I want to keep the name.

What are the rights, privileges you want for Tiffany and future generations? How do you want them to be taken care of?

• Matt: What’s the point of working this hard if you can’t have nice things? But on the flip side, do you really need all of those things? I want to hand down the lesson of past a certain amount, it’s just not that useful. Each new generation should do what’s best for their kids. But most of the wealth is not needed. We live a nice life, and sometimes, when it’s useful, we can fly private. We need to balance the push and pull of those two things.

Are there certain rights or roles Tiffany should have?

• Matt: Be it Tiffany or anyone else, the FAB needs to lead with compassion. Who are the people around us with the raw horsepower and business understanding to balance compassion, multiple stakeholders, and the corporate and global benefits. Tiffany is great at synthesis and understanding, but she doesn’t have the business background. Tiffany might represent the family- but she’s not the only voice in the conversation.

Do you have any divergent values?

• Matt: It seems like there’s a life curve, and ours are the same. I’m at an earlier point, so I care more about accumulation, and about holding on to what we’ve built. Joe thinks more about de-accumulation and bringing others in.
• Joe: You might call it the “accumulation stage” but I might call it the “proving yourself” stage. I’ve got one immediate family member: Matt. And now we have Tiffany. For me, my relationship with Matt is more important than the business stuff.

It sounds like you do have a system for conflict or at least a level of awareness about what’s important and whether you should step up or step back. Right?

• Matt: We rarely have conflict, but that means that we haven’t built that muscle. At Commonwealth, the closest we’ve come to conflict were disagreements relating to urgency: personnel, for example. In the past, I deferred to Joe because it was his company. And then Joe asked me to step up and take on more responsibility. But we’ve never been head-to-head on views. We usually give in when one of us doesn’t have a strong feeling or opinion on a topic.
• Current system to handle debate is retreating to the private sanctum.
• Joe: And if we can’t get a clear consensus, we’re missing something. We’re both smart. We both have experience. Theoretically we should have the same view, but we don’t. Why is that?

Are there values or traits in leaders that you want around you?

• Matt: I’m more likely to work within high-level frameworks. Joe might focus more on the person.

Have you and Tiff talked about what kind of parents you want to be?

• Matt: We have and we haven’t. We have similar values. Kids are the thing you can’t comprehend until they’re there. There’s a lot to learn on the way. One memory I have from being a kid is shopping with my mother at Marshalls, and this shared family love of finding a deal and understanding and appreciating value. It wasn’t just “this is cheaper”, it was about creating joy in understanding value.

What would be your “unfinished business”?

• Joe: Maybe nothing. It’s just a game. We’re here, we give it our best shot and hopefully we transcend into whatever is higher.
• Matt: I think if you passed tomorrow, it would be for me to help to launch Elevate.
• Joe: I want to have some parameters to make sure the money doesn’t hurt people, but I have full confidence Matt will carry on.

What happens if we get to a generation that isn’t competent?

• Joe: Carve out something for them, but not so much that the world is suffering while we wait for some kid’s kid, hoping that they’re confident and compassionate. I think we can plant more seeds now.

Are you separating a kid of competency and value system for future generations or in financial stewardship for the operating business?

• Matt: I think I am. The Deitch family molds one generation at a time. We’re going to make the next generation really strong, and then it’s up to them to make the next generation really strong. Joe’s whole focus was “Matt, be happy.” A lot of the people I went to school with had big advantages who are now realizing that they would have made different choices.

Do you have a singular regret?

• Joe: I wish I started martial arts when I was a little kid. I should have started therapy when I was younger. A few lessons were hard learned. But overall, I’m happy. In regards to the martial arts: I grew up in a rough neighborhood, and I think it’s essential for humans to learn how to defend themselves. But it also teaches respect. Every year for his birthday, I’d do the I-Can-Do-It-athon for Matt. It was a good stretch challenge, but something doable, to increase his capabilities and self-esteem. I wanted him to do a triathlon, not just to do it but to know you did it. To train and plan and build a love of health and exercise. Martial is similar, Tai Chi for example, it’s about understanding your energy, how to center yourself, and how to neutralize or direct the other person’s energy. That’s just a great metaphor for life.

What are the other traditions?

• Deitch Family members are great sleepers and can sleep anywhere and are great test-takers.
• Joe: Very conscious parental programing. So many people I know have irrational fears, that are actually their parent’s fears. Matt is a sapling. I don’t want to control him. I want to help him grow, and get strong, and have a good sense of self, good set of skills.

What capabilities would you like to learn to better run the business?

• Matt: It’ll be exciting and interesting. I’d also like to get better at golf.

On philanthropy, the Elevate Prize recipients are doing amazing things but it’s more on the left side of politics. Is that intentional?

• Joe: I’ve always been independent – why bend the knee for anyone? Just do the smart thing. 95% of friends are socially liberal and fiscally conservative. Recently, Republicans are reprehensible on a good day. And Democarts… maybe San Francisco is an example of taking liberal policy too far. I think when you are trying to make the world better and want to improve healthcare, poverty, and incarceration, and cycles of bad shit, it tends to be more liberal. But Elevate Prize is global.
• Joe: One of the dangers with an instituation is that they can wield an extraordinary amount of power. I’ve seen it with the judges at the Elevate Prize. If you’re black or queer, or black and queer, I’ve seen it play out. It’s something I’m trying to structurally fix. We need a balanced point of view.

Perhaps there isn’t a G3, and the companies are divested, would you want the wealth to be in a forever foundation or shorter-term?

• Joe: I think it should be hybrid. 90% is dispersed in 10, 20 years, and 10% is forever. But that’s what should happen whether there’s a third generation or not. There’s a lot of people suffering today. Some kid shouldn’t be getting a ton of money 50 years from now while people suffer today.
• Matt: We can put assets to spur growth and opportunity now. We identify each pod within the network, they could get a fraction of the wealth and THEY could decide what to do with.
• Joe: To my mind, when you’re giving people money, it can easily change the dynamics of the relationships. I want to be on the same level as people, so we can be friends. I don’t want to be beholden to me. There shouldn’t be an expectation to hand money out. It used ot be that you’d hoard your money until you died, but I realized that giving the money out earlier makes a bigger impact. I’ve started giving money or concierge medicine or educational expenses, and it has been really appreciated.
• Matt: If we just give money out, it can inhibit muscle-building, understanding.

How do you come to the decisions on the levels of giving? One person might not need it, another person might not use it. What factors does the FAB need to consider?

• Joe: I give a little more to Robbie’s sister than the other cousins but try to be mindful of treating her two daughters similarly. We’re figuring it out. Tempted to give Roz and Mark to give $5M and have them disperse to their kids how they see fit.
  • Everyone will find out everything. In the office, people only care about how much they make in relation to the person next to them. If you’re working as hard as them and they’re making more, it’s insulting. It’s not fair, it’s not right. I’m trying to protect myself against those things.
  • I’m not concerned in a Deitch Dynasty, but I want to create an institution like Commonwealth, focused on quality and community. When I think about the future, it’s about being a nurturing force, as opposed to some kid with my DNA years from now.

What are the cautionary areas related to wealth?

• Joe: you used to hoard money until you die and then some executor would give it out. I don’t want to do that. I started giving people a million when they turn 70. Certain people get $134,000 a year. Some people get concierge medicine. It’s appreciated. You’re giving people a peace of mind.
  • What are the watchouts? Beware the yardstick- people measuring up to each other. Making a gift relative of others makes sense. Over-giving with no muscle and no reason can lead to unhappiness.
  • In fighting, doubt and greed slipping into the system is something to watch out for.
  • We invite family and cousins to Abaco for Thanksgiving. It’s a week of Thanksgivings- every night. It’s an expense but helps to build community.
  • I’d rather give the money to charity than fly my family down to Abaco on a private jet – but I have enough money to do both!
  • Trying to change some long-held positions of mine that no longer make sense. An organization needs to be fluid.

Is there anything you worry about?

• Joe: age!
• Matt: nothing specific but as we start to move to guidelines, flexibility is important. Importance quality of life, customer quality of life,

What are the downside risks to technology?

• Regarding ChatGPT and other generative AI tools: if you have access and they save you time, use them, unless doing it on your own brings you joy.
• Matt: Pace of change is a risk, as a is fraud and bad actors.

What are the most important risks you face?

• Cybersecurity
• AI
• Identify the trends and try to stay ahead of it.
• Yuval Noah Hararis – the human species is going away.
• Pace of change
• Fraud
• Bad actors (can be within the family system)
• Value system – not transmitting the value system or choosing to adopt a different value system.

When it comes to the idea of next gen, who do you admire?

• Joe: Bill Gates and Andrew Carnegie
• Matt: what type of value is going out there? I’m looking for

What’s the most interesting project you’ve done?

• Joe: Starting Commonwealth was a big deal. Starting Elevate was a big deal. Writing the book.
• Matt: I’m more interested in for-profit projects. Finding new ways to reinforce connection. The venture side- exposure to all the new, crazy ideas.
• Funding
• Life adventures – moving to the Virgin Islands after graduation. Getting married, etc.
• Matt: DJing